WHERE'S YOUR SKIN IN THE GAME?

Preserving generational wealth is never accidental.

3 out of 4 family offices fail to reach the second generation, and 9 out of 10 don’t make it to the third.

That’s not bad luck—it’s structural failure.

But here’s the issue:

The logic behind how skin in the game is evaluated often breaks down.

There are 4 places where the thinking falls apart—not just in theory, but in practice.

1. Double Standards

Most investors we meet who demand skin in the game don’t apply that logic consistently.

They require co-investments in private real estate deals, but at the same time, are holding millions in public equities or funds led by executives with zero personal capital at risk.

C-suites with no “skin in the game”, but large base salaries and asymmetric upside compensation.

Even more often, that capital is traded in blind pools, with investments chosen by analysts they’ve never met, or managed by fund operators earning 5–10x more in annual fees than the nominal equity they hold.

They make those investment decisions on track record and potential upside, exclusively.

I’m not saying the structure is wrong.

But the double standard with real estate is.

2. Capital Aggregator ≠ Operator

There’s also a difference between capital aggregators (like many syndicators) and real operators.

If someone is raising capital to hire a third-party manager—fine. Ask about skin in the game.

I’d even go as far to say that their level of investment should far exceed what they earn from fees on the hold.

But when you’re dealing with a real operating sponsor, they’re already all in.

Time, reputation, infrastructure—that is real skin in the game.

And by cutting out intermediaries and vanity co-investments, all parties can often get sharper economics and stronger alignment on opportunities.

3. Transaction ≠ Partnership

Too much capital is deployed into transactions.

Not partnerships.

The best partnerships aren’t built on short-term projections or what was returned on the latest milestone.

They’re about trust, alignment, and shared ambition—the real foundation of generational wealth.

4. Capital ≠ Conviction

What it takes to build wealth is often aligned with what it takes to preserve it.

More often than not, they go hand in hand.

But sometimes, they’re in tension.

And when an investor fixates on modeled downside, at the expense of understanding the character of the deal itself, they miss the whole point.

Not all asset classes are created equal.

Every real estate asset class has its own operational profile.

A multifamily, office, self-storage, or single family rental deal doesn’t require the same operational lift a boutique hotel or luxury short-term rental.

Without accounting for the difference in complexity, execution risk, or day-to-day involvement, that’s not alignment—that’s misapplied convention.

Risk can be managed.

But conviction can’t be spreadsheeted.

And capital that’s overly preoccupied with vanity co-investment doesn’t strengthen the deal—it will drag it down.

I don’t believe capital is the only (or even the best) way to demonstrate conviction in a potential deal or partnership.

Because capital only reaches its full potential when paired with execution.

We’ve spent years building trust, credibility, and a track record that speaks for itself. Every investment puts our name, time, and expertise on the line.

We’re all in.

And opportunity cost is real.

That’s why we’re highly selective about the properties we take on—and the partners we work with.

We focus on alignment where it really matters:

a) The quality of the deals we take on

b) The results we deliver through disciplined execution

c) The quality and resiliency of the properties themselves

Many CRE models cracked under this last economic cycle.

4 out of 5 asset classes in the NPI have been in the negative since the COVID pandemic.

Yet throughout that same period—before, during, and after the downturn—luxury SFL assets under our stewardship didn’t just hold their value; they thrived.

Luxury SFL has proven to be one of the most resilient real estate asset classes, offering a natural hedge against volatility in other commercial real estate sectors.

Truly exceptional and well maintained properties benefit from greatly accelerated CAGRs that operate independently of yield, creating risk-adjusted returns that most traditional real estate investments can’t match.

But what sets our deals apart isn’t just the strength of the asset class—it’s how we structure them.

Our model is built to hold and operate exceptional properties—indefinitely.

The best returns don’t come from cycling in and out of commoditized deals, or losing gains to taxes and time between trades.

Our partners prioritize:

• simplicity

• generational wealth

• tax efficiency

• maximizing the compounding effect over time

• the flexibility to choose their deals, and

• the ability to deploy more capital into a strong pipeline of high-value opportunities

Jack Laurier is not a fund.

We structure and operate standalone property partnerships, focusing exclusively on unique, experiential hospitality assets.

By cutting out intermediaries to create sharper economics and stronger alignment,  enabling our property partners to invest in high-performing, risk-adjusted luxury vacation rental deals—without the constraints of traditional pooled real estate investments.

We do well only when our properties generate cash profits and grow, keeping our focus on asset-level value creation rather than constant fundraising

We take no share of net cash flows or refinance proceeds, and only participate in profits after our partners receive 100% of their capital back. 

We eliminate early downside risk by avoiding debt until stabilization. Each asset stands on its own fundamentals—not financial engineering.

Strategic recapitalization (no fees on refinancing) lets us accelerate IRR and enhance returns without increasing risk.

The result: true alignment, and disciplined execution at every stage.

This conservative structure, paired with the resilience of the asset class, creates a level of security that is truly rare in private equity real estate.

2025 marks 16 years in luxury real estate and vacation rentals for me, with experience spanning nearly every vertical in the space—from platforms and advisory to operations, asset management, marketing, and acquisitions.

Assets under our stewardship have achieved Gross Rent Multipliers as low as 4x, Gross Margins above 50%, and double-digit cash yields.

If we just consider the 4 most recent luxury properties we’ve taken on:

4 different properties, 4 different countries, 4 distinct markets.

Each ranked in the top 1% of highest-grossing homes in its region.

The odds of that happening by chance?
1% × 1% × 1% × 1%—a vanishingly small probability that it’s luck.

I can say with conviction: we know how to replicate success.

Our proven marketing and asset management frameworks deliver a return profile that few can match.

They’re predictable, repeatable, and they work because they’re built on timeless principles of luxury real estate.

But these aren’t isolated results.

Our team has 25+ years of combined experience, operating over $150M in luxury SFL real estate, spanning 36 markets throughout the Americas, Caribbean, Europe, and Southeast Asia—building deep expertise in every phase of the luxury SFL investment cycle

The difference is discipline—applied globally, executed locally.

That’s the advantage we bring, and where others fall short.

We’re not interested in working around property defects, extended maintenance delays, or uninspired assets. 

And we’re not going to market properties that lack vision or waste time debating over essential value-add improvements in building systems, design, FF&E, or OS&E.

In our world, there’s no value in half-measures.

We require a base fee and minimum CAPEX in every deal. Anything less compromises execution with disproportionate risk, and we don’t operate that way.

We focus on exceptional properties—those that deliver enriching, memorable experiences to even the most discerning guests.

Rare, beautifully crafted spaces in picturesque settings, filled with gratified guests who are willing—and happy—to pay market-leading ADRs.

We work with partners who understand that.

Who see that quality deal flow and a proven track record matter more than performative co-investment optics.

Who recognize that that selecting the right asset is as critical as the deal itself.

And who value aligning early with a team built for the long game—disciplined, experienced, and thinking decades ahead.